Brutal Bermudian Beauty: Reliving the 2017 Devil’s Isle Challenge

Two years ago when Plastic Tides co-founders Christian Shaw and Gordon Middleton told me they’d just completed the first unsupported SUP circumnavigation of Bermuda--a 20-hour, 40-mile, overnight endeavor--I thought they might be crazy. When they told me the experience inspired them to create a SUP race along that very course--the Devil’s Isle Challenge, officially the world’s longest open-ocean SUP race--I no longer thought they might be crazy. I knew. Then last weekend I found myself sprinting off the start in the second annual Devil’s Isle Challenge alongside SUP superstar Annabel Anderson, Oracle Team USA skipper Jimmy Spithill and a handful of other worthy watermen and women, and I realized: Plastic Tides is on to something here. That, or I’m a little crazy, too. Probably both.

Good morning, Bermuda!

It was 5am and dark and the wind bent the palm fronds out to sea at Snorkel Park in the Royal Naval Dockyard, ground-zero for the 2017 Devil’s Isle Challenge. It felt almost criminal to be up so early in such a sleepy, luxurious town. And with relentless 25-knot winds forecasted to blow whitecaps all day from the south, the vacant Bermudian sea didn’t exactly scream “paddle me!” Yet there we were, prepping our boards for a predawn start.

The competition was an eager lot of formidable paddlers, many flown halfway around the world for a shot at the Devil’s Isle. There were East Coast racers Garrett Fletcher and Andrew Dima, Julieta Gismondi and LouAnne Harris of the Atlantic SUPer Girls, Justin Schaay, Frank Fifils, Darrell Horton, Zach Rounsaville, and a small group of ambitious locals. And then there were the aforementioned celebrities: five-time Carolina Cup champion Annabel Anderson and Jimmy Spithill, ringleader of the Oracle Team USA, the prestigious sailing operation that holds the titles for both of the last two America’s Cups. With the 2017 America’s Cup coming to Bermuda in three short weeks, Spithill figured a 40-mile paddle race would make good competitive practice. The guy is an animal.

The Challenge also offered surfski and relay classes, with surfski stalwart Nathan Humberston threatening the sit-down division and Oracle grinder Graeme Spence and chase-boat operator Revelin Minihane teaming up to relay. The Oracle guys asked me to join their team--a stroke of luck that might actually get me through the Devil’s Isle. I obliged.

Even with perfect conditions, a 40-mile circumnavigation of the infamous island is a long shot for most paddlers. With the wind honking as it was, the feat was damn near impossible. Shaw and Middleton made the right call by adjusting the course to a more sheltered route through Bermuda’s Great Sound, a 30-mile circuit hugging the lee of the island to dampen the impact of the wind. Even still, I was nervous at the start line. I pushed out the prospect of fatigue, of being blown out into the Bermuda Triangle, and buried them with the positive: this was an adventure. This race, organized to raise money for Bermudian youth and oceanic conservation, was something I’d come a long way to be a part of. This was an opportunity to test myself and to do good for the world. It was all happening.

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The sun teased the horizon and turned the sky from black to orange as we heaved off the start line together into rivaling wind. Within half a mile the pack was scattered in chaos. Support boats weaved in and out diligently monitoring safety as nearly half the pack dropped to its knees and bucked through the chop, chugging at what felt like a snails pace toward the distant lee of the first segment. Multiple racers dropped out within the first five miles. Annabel Anderson shot off like a rocket and Spithill sunk into a steady rhythm, looking at home in the mayhem. I was relieved by my relay teammates 30 minutes into the race and I couldn’t have been more relieved. To the brave men and women going the distance solo, my cap is off. And for the next seven hours, so went the Devil’s Isle Challenge.

In the end Anderson finished first (see also: total domination) with a time of 6:02:05, more than eight minutes ahead of Spithill, who took second-place line honors on his 17′ unlimited. Behind him came Garrett Fletcher for first-place in the Men’s 14′ division. The rest of the group trickled in over the next few hours with the final two paddlers to finish landing just shy of ten hours from the start. Three paddlers didn’t finish at all. All paddlers celebrated.

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The Devil’s Isle Challenge was something different. Beyond the harrowing test it represents, the $13,000 prize purse and the personal prestige of competing, it brought us back to the true reasons we do this: adventure, trial, community and the ocean. Giving back to the environment and spreading our love for the sport. It gave us one hell of a memory to carry home. And isn’t that what paddling is all about. -MM

Big thanks to Christian Shaw, Gordon Middleton and Hailey Wilson of Plastic Tides, without whom the Devil’s Isle Challenge would not have been as it was.